Martin Shkreli's journey from pharma exec to Inmate #87850-053

Peter Foley/Bloomberg

Photographers take pictures of Martin Shkreli, former chief executive officer of Turing Pharmaceuticals, as he exits federal court with his attorney Benjamin Brafman, left, in the Brooklyn borough of New York on Aug. 4, 2017.

Patricia Hurtado

Bloomberg

March 8, 2018 12:58 pm Updated: March 8, 2018 12:59 pm

Martin Shkreli burst on the scene as an enfant terrible, a securities savant who was working on Wall Street at 17, set up his own hedge fund at 23, and launched the biotech company Retrophin after teaching himself biology.

Some may remember him as the trader who shorted drug companies after trash-talking them. Or the pharma executive who came under withering criticism for raising the price of a life-saving medication more than 5,000 percent. President Donald Trump labeled him a "spoiled brat," while the campaign of Democratic presidential candidate Bernie Sanders called him a "poster boy for drug company greed."

Shkreli, 34, now faces his day of reckoning Friday when he's sentenced by U.S. District Court Judge Kiyo Matsumoto in Brooklyn, New York. She'll decide whether to grant Shkreli's request to get as little as a year in prison or the 15-year-or-more sentence that prosecutors say he deserves for having lied to investors in his hedge funds and illegally controlling Retrophin shares.

For Shkreli, the road to prison began on a grey December dawn in 2015 when FBI agents swooped in to his midtown Manhattan apartment and arrested him on securities fraud charges. News cameras clicked and rolled capturing Shkreli, in a grey hoodie but minus his usual smirk, on his perp walk that morning.

Despite proclaiming his innocence and vowing to be vindicated, Shkreli was convicted in August of defrauding investors in two hedge funds with his lies and the Retrophin share scam. He was acquitted of looting Retrophin.

Shkreli emerged from court declaring his prosecution was a "silly witch hunt." In a Facebook live stream the same evening, he predicted he wouldn't spend a day in prison.

That was wishful thinking, even though some of Shkreli's victims didn't actually lose their investments, and made substantial profits in the end. Shkreli wound up in jail in September - about a month after his fraud conviction, when he issued a bounty for a strand of former Secretary of State Hillary Clinton's hair and the judge concluded he posed a threat. The judge said Shkreli actually cost his victims $10 million.

"The fact that he continues to remain unaware of the inappropriateness of his actions or words demonstrates that he may well be an ongoing danger or risk to the community," Matsumoto said in ordering Shkreli to remain behind bars while awaiting sentencing.

Since then, the judge hasn't shown any inclination of going easy on Shkreli. On March 5, she ordered him to turn over to the government almost $7.4 million in profits made from his crimes. That's what the government had asked for and far more than the $500,000 Shkreli proposed as the maximum appropriate penalty.

The Shkreli saga has been fodder for New York tabloids, and followed closely by his fans and haters alike on the internet, whether via his inflammatory Twitter postings that eventually got him banned from the site or the live streams on Facebook and YouTube from his apartment.

Here are some of the highlights (and lowlights) from the three years Shkreli spent in the spotlight.

- Shkreli faced criticism for hiking the price of Daraprim to $750 a tablet from $13.50 in 2015. He later said he probably should have charged even more.

- In early 2016, Shkreli was called before Congress to explain his actions. He refused to cooperate. Once out of the committee meeting, Shkreli tweeted: "Hard to accept that these imbeciles represent the people in our government." His Twitter account has since been suspended.

- Following his conviction for securities fraud and conspiracy in August, Shkreli mocked his trial in a press conference outside the courthouse.

- Back home, he streamed a chat with a New York Daily News reporter, complaining about fake news.

- After spending a few months behind bars, awaiting Friday's sentencing, Shkreli said in a letter that "Jail has some redeeming qualities."